Process for producing 1-benzoylamino-4-chloroanthraquinone



Patented Aug. 5, 1930 were sTA'rss WILLI HARTMANN, orwrasnonr-on-rnn-nnrnn, GERMANY, assrenon TO GENERAL.

PATENT OFFICE A ANILINE WOBKS,INC., OF NEXV IORK, N. 'Y., A CORPORATIONOF DELAWARE PROCESS FOR PRODUCING 1JEENZOYICAMINO-4-CHLOROANTHRAQUINONENo Drawing; Application filed December23, 1927, Serial No. 242,280, andin Germany December 22, 1926.

m quinone is carried out with extraordinary ease by the actionfofchlorine or substances yielding chlorine, such as for example,sulfurylchloride, on 1-benzoylamino-anthraquinone in nitrobenzene assolvent and if desired in the presence of suitable catalysts,e. g.iodine and ferric chloride. p

The temperature at which reaction takes place may vary in wide limits,e. gfiI have found that the reaction slowly takes place at ordinarytemperature, the mostfavourable temperature for performing the reactionhowever being 507 C. but the reaction can also be effected at highertemperatures. p

The following examples will illustrate my invention:

Example 1. grams/of l-benzoylaminoz'ene as solvent with a chlorinatingagent in anthraquinone are suspended in 2'00 grams of nitrobenzene, 126grams of sulfuryl chloride are added and the reaction mixture 1s stirredfor 15 hours at 60 C. On cooling thel-benzoylaminol-chloroanthraquinone, which has separated. is filteredand washed with alcohol.

E ma0npZe2.-5O grams of l -benzoylaminoanthraquinone arestirredin't'o200 cc. of nitro- 5;; benzene and chlorine is caused to pass'throughthis suspension at 60 C. The working up of the resulting product iscarried out as'in Example 1.

Example fi -34 grams of a-amino-anthraea quinone are suspended in 17 2cc. of nitrobenzene, 25.8 grams of benzoyl chlorideareadd'ed and thereaction mixture is heated to 120 C. for onehour. After cooling to 60(1, 84

ence ofiodine as catalyst.

I claim 1 1. Theprocess of producingl-benzoylamino-t-chloro-anthraquinone which rocess comprlses reactingupon l-benzo-ylammo-anthraquinone with sulfurylchloride in nitrobenzeneas solvent at about 60 C. in the presence of iodine.

2. A process which comprises reacting, upon 1-benzoylam1no-anthraq umonein nitrobenzene as solvent with a chlorinating agent.

3. A process which comprises reacting upon l-benzoylamino-anthraquinone,in nitrobenzone as solvent with a chlorinating agent at a temperaturebetween 5070 C.

4. A process which comprises reacting upon 1-benzoylamino-anthraquinonein nitrobenzene'as solvent with a chlorinating agent in the presence ofa catalyst favorable to-chlori-- nation.

5. a A process which comprises reacting upon1-benzoylam1no-anthraquinone in nitrobenzene as solvent with achlorinating agent at a temperature between 50-70 C. in the presence ofa catalyst favorable to chlorination. 6. A processWhich/comprisesreacting upon l-benzoylamino-anthraquinone in nitroben-v the presenceofiodine as catalyst.

7. A process which comprises reacting upon l-benzoylaminoanthraquinonein nitrobenzene as solvent with a chlorinating agent at a temperaturebetween 5070 (linthe pres- In'testimony whereof I have hereunto set myhand.

a 7 DR. WILLI HARTMANN.

grams of sulfuryl chloride are added and the 7 it temperature maintainedfor 15 hours. I The 50 quickly. Y Y

